PhytoHub: Showing entry for Glycyrrhetinic acid 3-O-glucuronide

Glycyrrhetinic acid 3-O-glucuronide

Identification

PhytoHub ID

PHUB000948

Name

Glycyrrhetinic acid 3-O-glucuronide

Systematic Name

Not Available

Synonyms

3beta-monoglucuronyl-18beta-glycyrrhetinic acid

CAS Number

Not Available

Average Mass

646.818

Monoisotopic Mass

646.371697939

Chemical Formula

C₃₆H₅₄O₁₀

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

InChI Key

HLDYLAJAWSKPFZ-HBKAJLBFSA-N

InChI Identifier

InChI=1S/C36H54O10/c1-31(2)21-8-11-36(7)27(34(21,5)10-9-22(31)45-29-25(40)23(38)24(39)26(46-29)28(41)42)20(37)16-18-19-17-33(4,30(43)44)13-12-32(19,3)14-15-35(18,36)6/h16,19,21-27,29,38-40H,8-15,17H2,1-7H3,(H,41,42)(H,43,44)/t19-,21-,22-,23-,24-,25+,26-,27+,29-,32+,33-,34-,35+,36+/m0/s1

SMILES

[H][C@@]12C[C@](C)(CC[C@]1(C)CC[C@]1(C)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O[C@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C(C)(C)[C@]3([H])CC[C@@]12C)C(O)=O

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.06e-02 g/l
LogS (ALOGPS): -4.78
LogP (ALOGPS): 3.97
Hydrogen Acceptors: 10
Hydrogen Donors: 5
Rotatable Bond Count: 4
Polar Surface Area: 170.82
Refractivity: 166.54920000000004
Polarizability: 70.9547068423391
Formal Charge: 0
Physiological Charge: -2
pKa (strongest basic): -3.686499495698764
pKa (strongest acidic): 3.5367642642030934
Number of Rings: 6
Rule of Five: No
Bioavailability: Yes
Ghose Filter: No
Veber's Rule: No
MDDR-like Rule: No

External Links

PubChem: 49822197
PeakForestCompound: 000721

Taxonomy as Metabolite

Family: Terpenoid metabolites
Class: Triterpenoid metabolites
Sub-class: Not Available

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
Glycyrrhizin	Terpenoids	Triterpenoids	Saponins	Show Food Phytochemical

Classyfire Taxonomy

Kingdom Name: Organic compounds
Class: Prenol lipids
Super-class: Lipids and lipid-like molecules
Sub-class: Terpene glycosides
Direct Parent Name: Triterpene saponins
Alternative Parent Names: ["Acetals", "Beta hydroxy acids and derivatives", "Carboxylic acids", "Cyclohexenones", "Dicarboxylic acids and derivatives", "Hexoses", "Hydrocarbon derivatives", "O-glucuronides", "O-glycosyl compounds", "Organic oxides", "Oxacyclic compounds", "Oxanes", "Polyols", "Pyrans", "Secondary alcohols", "Triterpenoids"]
External Descriptor Annotations: Not Available
Substituent Names: ["1-o-glucuronide", "Acetal", "Alcohol", "Aliphatic heteropolycyclic compound", "Beta-hydroxy acid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Cyclohexenone", "Dicarboxylic acid or derivatives", "Glucuronic acid or derivatives", "Glycosyl compound", "Hexose monosaccharide", "Hydrocarbon derivative", "Hydroxy acid", "Ketone", "Monosaccharide", "O-glucuronide", "O-glycosyl compound", "Organic oxide", "Organic oxygen compound", "Organoheterocyclic compound", "Organooxygen compound", "Oxacycle", "Oxane", "Polyol", "Pyran", "Secondary alcohol", "Triterpene saponin", "Triterpenoid"]

Spectra from Phytohub

Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Predicted LC-MS/MS	Not Available	Positive	low	View Spectrum	(87.00821896,0.4108001089);(99.00821896,0.560256786);(117.0187836,0.5961724674);(159.0293483,0.6521008067);(169.1228548,0.4843494817);(177.039913,2.1058448);(221.1541549,0.4471193143);(407.331391,2.586777161);(409.3470411,0.4144479311);(423.3263056,3.58598821);(425.3419557,2.472133236);(427.3576057,0.7071806068);(433.3106556,0.4306496836);(435.3263056,2.35639835);(439.3212202,0.7103231898);(441.3368703,0.9956010496);(451.3212202,1.47112125);(453.3368703,16.32632008);(455.3525204,2.161162644);(459.3838205,0.3845087931);(461.3994706,0.3845087931);(471.347435,17.21539813);(583.363479,2.57935394);(585.379129,0.6928989168);(599.3583936,0.5848964354);(601.3740437,3.884510138);(603.3896937,0.7413891407);(611.3583936,5.739486936);(629.3689583,0.5452217174);(629.3689583,15.57592399);(647.379523,12.19715592)
Predicted LC-MS/MS	Not Available	Positive	med	View Spectrum	(141.1279402,1.261859666);(159.0293483,2.424572383);(169.1592403,1.261859666);(177.039913,3.924174423);(209.1905404,1.016230461);(217.1228548,0.8304529661);(219.1385048,0.8473964796);(235.169805,1.236024864);(369.2429699,0.8399075667);(371.25862,1.017636534);(381.2793554,1.42445069);(385.27427,0.831359651);(385.3106556,1.218012149);(397.27427,1.266594564);(405.3157409,1.025121631);(407.331391,3.266335729);(409.3470411,1.224889208);(423.3263056,7.131360327);(425.3419557,6.531496278);(427.3576057,2.875739015);(435.3263056,3.169152323);(451.3212202,1.573738659);(453.3368703,21.03520595);(455.3525204,2.663221637);(471.347435,18.83506636);(583.363479,1.45943028);(601.3740437,1.974237535);(603.3896937,0.7995368246);(611.3583936,2.650450382);(629.3689583,3.314402233);(647.379523,1.070083566)
Predicted LC-MS/MS	Not Available	Positive	high	View Spectrum	(69.07042529,1.46648324);(87.00821896,2.396363324);(89.02386902,1.671035014);(117.0187836,1.732234816);(141.1279402,3.613398541);(155.1435902,1.528990768);(159.0293483,1.6177457);(161.0449984,1.905526714);(169.1592403,3.613398541);(175.1486756,2.365724412);(209.1905404,3.606541064);(217.1228548,1.840260374);(289.2167552,2.739424017);(317.2480553,2.739424017);(357.2793554,2.739424017);(367.2273199,1.634828159);(383.25862,1.923286745);(385.3106556,6.368501878);(395.25862,2.265891313);(395.331391,6.616132187);(399.2899201,1.733766318);(399.3263056,1.489630172);(407.331391,4.185108358);(413.3055702,1.529655689);(421.3106556,2.630185106);(423.3263056,12.48187306);(425.3419557,5.346082826);(441.3368703,2.224311435);(453.3368703,6.93737454);(455.3525204,2.245661832);(471.347435,4.811735826)
Predicted LC-MS/MS	Not Available	Negative	low	View Spectrum	(41.00273965,0.6632814172);(59.01330434,0.7341192062);(71.01330434,1.603091444);(87.00821896,1.472191884);(89.02386902,2.154525522);(103.0031336,1.399763801);(117.0187836,2.274703677);(147.0293483,1.827122043);(163.0242629,1.052842271);(175.0242629,1.325036879);(193.0348276,1.174731251);(407.331391,1.113306555);(423.3263056,1.5714731);(425.3419557,2.113746288);(449.3055702,0.9270644422);(451.3212202,7.989646541);(453.3368703,0.8373688332);(465.3368703,1.488873014);(469.3317849,15.94750437);(495.347435,1.302273909);(511.3423496,1.137937295);(527.3372642,0.7238721393);(555.3685644,0.8953529847);(557.3842144,1.454551327);(583.363479,3.667462158);(599.3583936,3.119175664);(601.3740437,5.900185803);(601.3740437,6.29324213);(615.3533082,0.6157358126);(627.3533082,4.533621186);(645.3638729,22.68619705)
Predicted LC-MS/MS	Not Available	Negative	med	View Spectrum	(43.01838972,1.148915608);(59.01330434,1.896472993);(73.0289544,1.405020455);(87.00821896,2.085991032);(89.02386902,1.905561723);(103.0395191,1.860963195);(117.0187836,0.9082143559);(131.0344337,0.9522611639);(145.0136983,0.9742292217);(147.0293483,2.391036332);(149.0449984,1.035193775);(175.0242629,2.762685622);(193.0348276,2.293116117);(407.331391,3.467764277);(409.3470411,1.65103042);(421.3106556,1.995497881);(423.3263056,6.590703175);(425.3419557,9.863463266);(451.3212202,5.51205849);(453.3004848,1.681011729);(453.3368703,1.011766149);(469.3317849,22.25931461);(555.3685644,2.213700702);(557.3842144,2.528754143);(583.363479,4.516822226);(583.363479,0.895687915);(599.3583936,2.205880923);(601.3740437,3.046429307);(601.3740437,3.058311489);(627.3533082,2.922611427);(645.3638729,2.959530275)
Predicted LC-MS/MS	Not Available	Negative	high	View Spectrum	(41.00273965,1.901325726);(43.01838972,4.032453052);(44.99765427,1.010403176);(56.99765427,0.9178681691);(59.01330434,5.82155059);(61.0289544,4.084237516);(71.01330434,1.53056442);(73.0289544,2.377468591);(84.99256889,0.5655877632);(87.00821896,1.297253708);(89.02386902,0.8345208137);(91.03951908,0.7007137948);(103.0395191,1.233416413);(117.0187836,0.4778017157);(131.0344337,4.226577904);(147.0293483,1.604131366);(149.0449984,0.726654579);(421.3106556,1.661261688);(423.3263056,8.255699255);(425.3419557,12.68806807);(437.3055702,1.173972478);(439.3212202,0.9172127715);(451.3212202,2.426584293);(453.3004848,2.066927642);(453.3004848,9.032687484);(465.3004848,0.5551853715);(467.3161349,2.282997704);(467.3525204,0.504965695);(469.3317849,23.87216);(539.3372642,0.7460994458);(555.3685644,0.4736488125)

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

	Food Phytochemical	Food Source	Food Source Group
	Glycyrrhizin	Liquorice	Confectioneries and desserts	Publications	Show

Role as Biomarker of intake

No roles as Biomarker of intake found

Metabolism

	Food Phytochemical		Metabolite	Species	Biofluids	Origin	TMax	CMax	Urinary Excretion	Formula	Monoisotopic mass
	Glycyrrhizin		Glycyrrhetinic acid 3-O-glucuronide	human rat	bile, plasma, urine	unknown	Not Available	Not Available	Not Available	C₃₆H₅₄O₁₀	646.371697939		Publications

Inter-Individual Variations in Metabolism

	Food Phytochemical		Metabolite	Effect	Value

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Showing entry for Glycyrrhetinic acid 3-O-glucuronide